I think you need to go back further to the education system. I’m a 1990s kid, so I grew up having teachers tell us to “think for ourselves.” In high school, a bunch of our teachers joined the students in protesting the administration over a (completely innocuous) dress code. GenX and millennials were positively marinated in anti-establishment, anti-institution rhetoric growing up. The Joe Rogans of the world are a predictable result of that education.